(3beta)-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl) oleanolic acid - Compound Card

(3beta)-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl) oleanolic acid

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(3beta)-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl) oleanolic acid

Structure
Zoomed Structure
  • Family: Plantae - Sapindaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Sterol Glycoside
Canonical Smiles OCC1OC(O[C@H]2CC[C@]3(C(C2(C)C)CC[C@@]2(C3CC=C3[C@@]2(C)CC[C@@]2(C3CC(C)(C)CC2)C(=O)O)C)C)C(C(C1O)O)NC(=O)C
InChI InChI=1S/C38H61NO8/c1-21(41)39-28-30(43)29(42)24(20-40)46-31(28)47-27-12-13-35(6)25(34(27,4)5)11-14-37(8)26(35)10-9-22-23-19-33(2,3)15-17-38(23,32(44)45)18-16-36(22,37)7/h9,23-31,40,42-43H,10-20H2,1-8H3,(H,39,41)(H,44,45)/t23?,24?,25?,26?,27-,28?,29?,30?,31?,35-,36+,37+,38-/m0/s1
InChIKey VRFWJSCLROXBBW-NZSRVEMDSA-N
Formula C38H61NO8
HBA 7
HBD 5
MW 659.91
Rotatable Bonds 5
TPSA 145.55
LogP 5.2
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 659.44
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Paullinia pinnata Sapindaceae Plantae 290984
2 Paullinia pinnata Sapindaceae Plantae 290984

Showing of synonyms

  • Lunga PK, Qin XJ, et al. (2014). Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata.. BMC complementary and alternative medicine,2014, 14, 369. [View] [PubMed]
  • Lunga PK, Tamokou Jde D, et al. (2014). Antityphoid and radical scavenging properties of the methanol extracts and compounds from the aerial part of Paullinia pinnata.. SpringerPlus,2014, 3, 302. [View] [PubMed]
Pubchem: 145999357

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 659.91 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 659.91 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 659.91 g/mol

Antimicrobial
Antityphoid

Absorption

Caco-2 (logPapp)
-5.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.17
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
32.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.57
Plasma Protein Binding
85.56
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.43
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.61
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-61000.59
Rat (Acute)
2.74
Rat (Chronic Oral)
2.71
Fathead Minnow
90.55
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
3592.98
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.8
Log(P)
5.24
Log S
-5.06
Log(Vapor Pressure)
-109.27
Melting Point
289.48
pKa Acid
5.04
pKa Basic
7.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7115

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